It was to be my last summer of freedom before I started college. My sister Laura, a year older than me, had taken a year out, some worldwide paid modelling gig, so was going to be starting the same year but she was going out of state and I decided the local technical school would start on the career path I wanted.
Laura and I got on okay, with her being the pretty model growing up I was in her shadow a lot. She'd be taken to beauty pageants, photo shoots and I'd always felt I had to try twice as hard to get half the attention she got growing up. I didn't blame her, it took a huge stress out crash for our parents to dial it back and finally let her go her own way.
I was sitting in my room quietly reading a gaming magazine when I heard Laura having a pretty heated conversation on the phone. We shared an adjoining bathroom (or rather, I had a tiny window I could use said bathroom in the mornings) and I'd forgotten to close my door.
"I told you I'd already fucking paid for it Brad, why do you all of a sudden not want to go? Wait, let me put you on speaker," she said, I could hear she was upset.
"Look, I'll tell you since you're going to find out anyway, last week I hooked up with Bethany, it kinda just happened and I want to see where it goes," he replied.
"What? Are you fucking kidding me? Last week when I had food poisoning and was in bed all week?"
"Well, yea, I got lonely."
"I should have listened, even your cousin thinks you're a piece of shit but I thought I knew better. Fuck you Brad, fucking asshole."
I heard a loud thump, assumed it was her phone being thrown then it went quiet. About ten minutes later she lightly knocked on my opened door and came into my room. Her eyes were red like she'd been crying.
"So I dropped my phone and it broke, can I please use yours, I need to try and cancel my flights to Cancun," she said.
"Why?" I asked.
"Please, like you didn't hear."
"I was trying not to be nosy, I'm sorry sis."
"Can I use your phone or not?"
"Yes but my new battery doesn't come until tomorrow, you'll have to use it on the charger."
"Fine."
She sat on my chair and dialed the number she had on a piece of paper.
"What do you mean I can't cancel... So if I hadn't pre-paid I could have but now you have my money it becomes hard luck? ... Fine, what about a replacement? ... Sure, I'll pay another $50 rather than lose $800, I'll call back," said Laura. "Fucking assholes. I need to make a few calls, can I take this to my room?"
"Sure but no getting mad and dropping that one,"
"That is so not funny," she said then left.
About an hour later, Laura came back into my room and quietly plugged my phone into my outlet with it's charger. She sat down in my chair again with a pained look on her face.
"Spit it out sis," I said. She hesitated a few seconds before she spoke.
"So, I've called all my friends. They all have plans and can't come with me, especially as such short notice. I don't mind spending $800 on one last party vacation before I go back to college but I'll be damned if I just let the money go to waste."
"And?"
"I want you to come with me."
"What? Why don't you just go yourself?"
"Mom and Dad won't allow it, they were fine if I was going with Brad."
"Who all is going?"
"A few friends from my instagram modelling group, we planned our first meetup."
"Sounds like something I'd totally enjoy." I said with heavy sarcasm.
"You'd get to watch a bunch of young models taking selfies in bikinis on the beach. Or help rub lotion on them, or watch them rub lotion on each other."
"You say that like I'm some kind of perv or something."
"Oh please, I've seen your browser history little brother, I don't judge or care. I promise you'll have a good time, I'll even give you some spending money."
"Fine but you owe me, I'll be missing the opening weekend of the new Marvel movie."
"I'll take you when we get back, not like you'll see any spoilers on the beach."
"You can tell Mom and Dad."
"Already have, I'll leave you to sort your clothes, Mom said you need new shorts so go shower and I'll take you to the store."
After shopping we got home in time for lunch and I was sent to wash all my clothes. I packed my case and sat watching a movie on my laptop. Laura knocked on my door and came and sat on my bed.
"I really appreciate you doing this for me. I know we'll have a good time," she said with a smile.
"Well isn't like I had to move a bunch of things off my schedule, you've always been so independent or fussed over by Mom and Dad, I hated seeing you upset that way."
"I guess I can make up for some of that with this trip, I know you were kind of left by the side because of me and I feel guilty sometimes, I talked about you with my therapist last week."
"I didn't know you were seeing one."
"There's a lot you don't know about me sweetie. Anyways, get a good sleep tonight okay, we're up at 4am."
Laura leaned over and kissed me on the cheek then left.
I took melatonin and was in bed pretty early that night, 4am still felt wrong but Mom and Dad were tired too and didn't fuss over us too much.
"Now son, I'm trusting you to look after her okay, don't be letting her wander off to beach parties without you, I don't care if you drink a little but one of you stay aware and look after each other," said Dad.
"I put some extra money in your bag sweetie, I know Laura gave you some spending money but I'm proud of you for helping her. Have fun okay!" added Mom.
We finally made it through security and sat in the boarding lounge, both sipping on the overpriced coffee. The flight wasn't too bad, the drive to the resort was pretty rough but we finally made it to the hotel and waited to be checked in. Laura had me wait with the bags while she got our room.
"You bring the bags sweetie, I'm going to get us some water," said Laura, smiling as she came back with our keys.
"Don't they have a concierge or something?" I replied.
"It's kinda off season sweetie, If we want to wait 40 minutes. There's an elevator, you'll be fine."
Laura led us into our room, I looked around and put her bag on the bed.
"Your room's nice, is mine next door?" I said, waiting.
"Um, this is our room sweetie. I was coming here as part of a couple remember. You can have the bed, I'll throw these couch cushions on the floor. I've slept on worse."
"No, I'll take the couch, it's fine."
I walked over and went to pull the cushions off but they were fixed.
"Well fuck," I said, showing Laura.
"So, I'll stick to my side, we'll have a row of pillows down the middle and we'll share the bed. Come on, it'll be fine."
Laura was pretty upbeat about the whole thing, I was a little concerned but brushed my fears aside.
"What about getting changed and stuff, we haven't shared a room since I was 5,"
"How many times have you walked into our bathroom to see me in just a bra and panties? Relax, we're here a week, I'll shower first in the mornings and while I put on makeup, you shower. I want you to have a good time okay, don't stress about this," she replied.
I took her advice and looked out of our window, the resort looked pretty cool, private beach, no kids and wasn't very busy. We changed into our lounging clothes and went to meet her friends in the lobby, one girl recognized Laura and greeted her with a smile.
"Hi! It's so good to finally meet in person, can't believe it's been 2 years!" said the woman.
"I know, have you heard from the others?" replied Laura.
"Yes, I have, you didn't get my texts?"
"No, I broke my phone."
"Well shit, you're waaay out of the loop. Amber, Kendra and Lucy aren't coming, is just us 2. I was coming with my boyfriend but he's on a fucking no fly list thanks to some posts he made online, those three thought it would be fine trying to bring weed on the plane so they were all arrested and not allowed to fly either."
"Wasn't Amber bringing the cameras?"
"She was, all I have with me is this 4 year old iPhone in case I lose it but I paid for this trip already, no way I was cancelling. We'll still have a good time, just more time drinking and tanning and less time taking pictures. Your poor boyfriend will be bored."
"Oh he'll be fine, he can go to the bar for us if the waiters are slow, won't you sweetie?" said Laura to me.
"Uh, sure."
The woman paused a second.
"So, I don't even know your name," she said.
"Shit I'm sorry, Maya this is my boyfriend Josh," said Laura.
"Well it's wonderful to meet you. I hope I don't become like a 3rd wheel, I was really expecting the guys to do their own thing but with just us I don't know what to do."
"We're all legal to drink down here, I vote relax and enjoy this weather," said Laura.
"Sounds like a plan. Let's go eat then see which bar is nicest."
We ate at the lunch buffet, the food was pretty good but I waited until Maya went to the bathroom before I said anything to Laura about my new status.
"What the fuck Laura, why didn't you tell her the truth?" I said, trying to keep quiet.
"I have managed to keep my shit together, I just found out my now ex boyfriend is a cheating asshole. I want to enjoy this trip and I want to do it without dealing with the emotions that will likely have me in tears until we get back. Let's call it a thank you okay? You play along and let me save face and I can keep myself from breaking down. Will you do that for me?" she said, I could see the pain in her eyes.
"Okay fine, sorry, it just caught me off guard. I'll do it for you."
"Thank you, I love you, I promise this stays between us okay."
"Okay, I love you too."
"Well that looked like a far too intense conversation to be having over lunch, you guys okay?" said Maya, we didn't see her coming back.
"Oh is nothing, Josh wanted to leave us to ourselves but I told him we could have fun together, I'd feel horrible leaving him alone," said Laura.
"Of course, we'll be the 3 gringo's, fuck the rest of those bitches, we'll take some crappy pictures, get drunk and make them regret not coming."
Maya was pretty fun, I stuck to soft drinks the first day but Laura got a little drunk and was still a bit bubbly when we got to the room. She brushed her teeth while I set up the line of spare pillows between us but when I got back from the bathroom when it was my turn, she'd thrown them onto the couch.
"I had half the space I like because of those things, I will pretend there's an imaginary line and I'll stay to my side," she said with a grin. I decided not to argue.
"Fair enough, I'm pretty tired though, goodnight," I replied, getting into bed.
"Hey, thank you for being here, I really do appreciate you doing this for me," she said then leaned over and kissed me on the cheek.
"You're fine, Maya is pretty fun."
Laura crashed out and was lightly snoring, I rolled over and was asleep pretty quickly. When I woke though she'd draped herself over me, her breasts pressing into my back and one of her legs intertwined with mine making my morning boner throb in my boxers. Laura woke up with a fright when I moved.
"Fuck, I'm so sorry," she said as she pulled away from me.
"It's fine, I don't remember you snuggling into me."
"I'll go shower, do you need to pee first?" she said, already out of bed.
"I uh, I'll wait."
Laura looked at me then her brain clicked, she just said 'oh' then got in the shower. Thankfully my cock had gone soft by the time it was my turn to shower, Laura was already dressed, well if you called the bikini she was wearing dressed and had a very light dusting of makeup on. She looked like she'd just towel dried her short blonde hair.
"I'm guessing Dad never saw that bikini, he'd be all 'you can't go out dressed like that young lady', you do look great though," I said with a laugh.
"I figured I might as well get my money's worth out of it, I couldn't wear this at home, would be Mom that freaked. You don't think it looks too slutty?" she said, giving me a slow twirl.
I had to remind myself again that she was my sister, the top was pretty thin but the bottoms were pretty much a g-string and showed me her full ass.
"It's uh, very nice, you're wearing your skirt shawl thing right?"
"It's called a sarong sweetie and yes I'll be wearing it."
Maya was a little hungover so was a little quiet at breakfast but once we got to the beach she perked up and the women were having fun chatting. A guy came over and tried to hit on Maya but she brushed him off.
"Sorry, I'm here with these two, they're a couple and I'm their sex slave, I'm not allowed to talk to anyone else," she said, he took the hint and left.
"You may have just made him worse, next he'll come back wanting to watch," said Laura with a laugh.
"Oh no way, last time I had a threesome the husband was supposed to just be watching but tried to fuck me when I was eating his wife's pussy. I shut that down pretty quick, she was sexy but he was a slob."
"You told me about that on messenger, you were so mad, I couldn't help laughing."
"Well it's up to you Josh, if I start kissing your girl to keep the boys away you can protect us."
"Oh he'll be too busy watching for himself," replied Laura, both girls were laughing pretty hard.
The conversation changed to makeup and lighting, I got bored just sitting around so I went to swim for a while then after we had dinner we went back down to the beach to sit at one of the fire pits. We had the beach to ourselves, all the other guests were at the mini concert by the main pool but we didn't like the music and took some beers to escape. I was still pretty sober but Laura and Maya were pretty drunk.
"So, I know I've only been around you both like a day and a half but I've not once seen you guys kiss or even act like a couple, what the fuck?" said Maya out of the blue.
"He gets really shy with PDA, he wouldn't even hold my hand in the airport. He shows me how much he loves me behind closed doors," replied Laura.
"Well, it's just me here, give him a big kiss."
"No, he'll get embarrassed and make him worse, we're fine, really."
"Fine but your girl is a hottie, Josh, need to claim that sexy ass of hers before these vultures think you're an escort or some shit. Fuck, I gotta pee again, I'm just going behind that hut."
Maya got up and went behind a nearby beach hut, when Laura was sure she was out of earshot she leaned close and whispered.
"Would you kiss me if I asked you to? Just once to throw her off, please," said Laura.
"Like on the cheek or something?" I replied.
"No, like you're kissing your girlfriend."
"This is getting we..."
Before I could say much more, Laura pulled me close and kissed me with passion my own girlfriend never had. I was stunned, I could taste the tequila on her tongue as it danced with mine. When she let me up for air, Maya had come back and was sitting grinning as she watched.
"Now that's a kiss, do that in front of that waiter that's been drooling over you, he'll back off," she said with a laugh.
"Or he'll spit in his food," replied Laura, laughing too.
I sat smiling, still in shock from the surprise kiss and hated to admit that I really enjoyed it.
"Well I am really fucking drunk and I think we should go on one of the excursions tomorrow, I don't want to be too hungover for it,"
We made sure Maya got back to her room okay then quietly walked back to our own, Laura was pretty quiet, she sat down on my side of the bed and was looking down at the floor.
"I... I'm sorry I did that, I hope you don't hate me," she said, I could see tears welling up in her eyes.
I should have been mad, I should have been on the phone about my own twisted sister kissing me to save face, instead I put a finger under her chin and kissed her softly on the lips then wiped the tear that ran down her face.
"The only thing I'm maybe, and I mean maybe, upset with is being called Josh. I would be a liar if I said I didn't enjoy it," I replied, she stood up and grabbed me in a tight hug.
"Thank you, I was so worried."
"We're fine, now go brush your teeth and let's get some sleep."
We both slept really well, I woke first while Laura was still fast asleep so I showered and woke her with a kiss on the cheek. She opened her eyes and smiled then got ready as I sat on the balcony. The excursion was fun, being off season it wasn't really busy but the guide really knew his stuff and made it fun and interesting. When we got back to the beach that night with our stash of booze, Maya seemed to be in just a feisty of mood from the night before.
"Well, I'm bored of just drinking, let's play truth or dare," she said, taking a big drink from her glass.
"I don't think that's a good idea, we're more drunk than Josh and maybe there's stuff I don't want a new boyfriend to know yet," replied Laura with a smile.
"Oh fuck that, you don't care do you Josh?" said Maya to me.
"I'm game," I replied.
The question started out innocently enough but Maya soon turned things sexual.
"So, Laura, have you ever had sex with a married man?" she said, grinning.
"Oh come on, that's a little darker than all my questions," replied Laura.
"Well?"
"Bitch!, dare," replied Laura, laughing.
"Hmm, I dare you to sit topless for 30 seconds."
Laura didn't hesitate, she untied her bikini top and sat topless.
I couldn't help but look, I'd been seeing her in barely there bikinis all day but to see her naked breasts, her beautiful pale nipples exposed to me in the moonlight, I was in awe. I knew trying not to think of her as a sexual being was lost at that point, my cock was starting to get hard by the time she had her top back on and I couldn't hide it very well.
"Well, Josh certainly approves," said Maya, grinning as she noticed me shift in my seat.
"Well, he's a breast man and mine are fabulous," laughed Laura.
"Shit, that security lady is headed this way," said Maya.
"My friends, I don't mind you guys being down here late, you cleaned up after yourselves last night but no nudity okay, my boss is an old prude and thinks even bikinis are too skimpy. Keep it to your room for me okay?" she said.
"Sorry Ma'am, we didn't think anyone could see us down here," I replied.
"They can't but the cameras can. Have a good night okay."
The girls laughed when she was out of earshot.
"Oh fuck, I see it now. Glad it isn't pointed that way, I peed behind that hut," said Maya, laughing again.
"I just hope she didn't take a screen shot." replied Laura.
"You had your back to it, could see you're topless but doubt the camera caught nipples," I said.
"Well I'm way too wired to go to bed, my room is closer," said Maya as she started gathering the beer.
We made our way to Maya's room, she had a nice suite similar to ours, she poured us all drinks as we got comfortable on her couches.
"So who's turn is it?" said Laura.
"Oh, we're still playing? I think Josh should have a turn," replied Maya.
"I'm kinda over truth or dare, I know what I need to about Laura and I'd never know if you're telling the truth or not Maya," I replied, trying not to sound like an asshole.
"Fine, dares then, I want to have fun, I was hoping to be with more people but you're stuck with me so come one grumpy pants, take a drink and make a dare," replied Maya.
"Okay, I dare you to sit topless for an hour," I said.
"Oh that's an easy one, I love showing these off."
To my delight, Maya pulled her t-shirt and bikini top off in one go and sat with her pert breasts exposed to me, her nipples were already hard, hers were slightly bigger than Laura's but not by much. My cock started hardening of course.
"So, I get to dare back right, I know you've seen Laura's breasts and now you can see mine, let's see what you have. I dare you to stand up, drop your shorts and give me a twirl," said Maya.I hoped that Laura would step in and put an end to the game but she didn't.
"Don't look at me, you started this, I'm not going to stop you," said Laura with a grin.
By then the excitement of seeing Maya topless coupled with the memory of Laura's breasts and the situation I was in had me really hard. I put it down to the drink loosening my inhibitions but I decided 'what the hell' and stood up, pulled my shorts down and stood facing the women, my hard cock sticking out in front of me. Laura sat with her mouth slightly open and Maya just grinned.
"Well shit, I'm surprised you don't walk with a limp taking that every night sweetie," said Maya.
"Oh I manage," said Laura, not taking her eyes off my cock.
"Can I uh, pull these up now?" I said, feeling myself go red.
"Not yet, final dare then we're done, I'm getting tired, Laura, I dare you to suck him for 30 seconds in front of me," said Maya.
I felt my heart pounding in my chest. Seeing my hot sister topless was one thing but having her touch me sexually was a line I figured she'd not cross and she'd have to come clean. Oh how wrong I was! She got up, got on her knees in front of me and while looking up at me, took the tip of my cock into her mouth and sucked me, circling the head with her tongue then taking more into her mouth. She sucked until I started to groan then looked over at Maya.
"That about 30 seconds?" she said as she pulled my shorts up.
"Uh, yes. I'll be picturing that while I play tonight. You should both go though, I want to go hiking tomorrow and don't want to be too hungover," said Maya.
Maya practically shoved us out of her room, Laura didn't seem to care, she took my hand and pretty much marched me to ours. She closed the door behind us and when I tried to talk she just pulled me to her and kissed me passionately. She pulled my shirt off, then her own then pushed me onto the bed and pulled my shorts off too.
"L... Laura, what are you doing, shouldn't we talk about this?" I stammered.
"Talk when we're done," she said.
Before I could say any more, she'd pulled her bottoms off and mounted me then took my entire cock into her pussy in one smooth move. I gasped in pleasure as the warmth of her pussy engulfed me, she paused, muttering 'oh fuck yes' then began to fuck me, riding up and down on my cock. She didn't last long, she took me to the hilt then with a few short thrusts, shuddered as she climaxed. She got off me then got up onto the bed on all fours and looked at me.
"I know you're close, cum in me, I'm on birth control," she said, still breathing pretty hard.
I didn't hesitate, we'd already crossed a line and I figured I might as well cum. I got up and pushed into her, managed about five or six thrusts then was cumming, groaning in pleasure as my cock swelled as it sprayed her pussy with my seed. I stayed in her until I was spent then collapsed in a heap with her on the bed.
"Y... Your cock is beautiful baby, I had no idea," she said, toying with my softening cock.
"Y.. you're not supposed to know, I'm your brother," I said without any real conviction.
"We're both adults, it was just sex, are you upset with me?"
"No, I should be, being told our whole lives incest is wrong and I shouldn't even be looking at you that way but they didn't say it would feel so fucking good. I love you."
"I love you too. I'm sorry, I just got so turned on when she made me lick you I needed to have you inside me."
"If you keep playing with my cock like that you'll get me going again."
"You're way bigger than my ex, we can go again if you're gentle, you on top."
We kissed as she stroked me back to hardness then she pulled me on top of her and I slid my cock into her again. I took it slow, savoring her tightness, the look on her face with each thrust and when we were both soaked in sweat and breathless, the look on her face as she climaxed. I sprayed what seed I had left in me into her on the peak of her orgasm then collapsed on top of her, resting my head on her shoulder as we caught our breath. She rolled me off her when I softened again and we just laid there, gazing at each other with a soft smile on our faces.
We both slept really well that night, we left an extra tip for the maid from the mess we'd made on the bed and next morning we acted like lovers, kissing, touching and holding each other before we shared a shower and finally dressed. We walked holding each other's hands and sat close as we ate breakfast.
"Wow, looks like I'm not the only one who enjoyed last night," said Maya as she joined us.
"What do you mean?" replied Laura.
"Oh please, you have a smile on your face that says 'I got it good last night' and so does he."
"Still want to go on the hike?"
"Oh, nice try, not changing the subject on me. We're going to have details on the hike."
"What do you want, we had sex, big deal."
"Enjoy your food."
Laura and I both wondered what was going on, Maya waited until we got to a secluded spot on the trail away from the guide then took Laura and I by the hand.
"So, 'Josh', how was sex last night? It was your first time with her wasn't it?" she said.
"What?" I replied.
"I'm going to come clean, when Laura and I had our video chat a few months or so ago, you came into the room. You were gone in a second or so but Laura was mid story, said 'Marcus, I'm on chat, I'll bring it later.' When I asked you said 'oh just my brother looking for his charger' then carried on with your story. It was hilarious, about you flashing the guy in the bmw and getting him pulled over or something, anyways, I know you're brother and sister," she said, smiling.
"What is this, set us up, let us fall into your trap then blackmail us, what's your angle here Maya," Laura replied, a look of rage in her eyes.
"Oh sweetie no, I'm sorry, really not where I'm going with this. When you told me he was your boyfriend I was confused but played along. I thought you were winding me up or something. When you took it further and kissed him I was very curious and excited. When you sucked him last night I almost came right then. Long story short and so you can relax those lazer eyes of death, I lost my virginity to my brother before he left for the military. We fucked for 3 weeks straight, his stamina was amazing. I fuck my uncle as much as I can, his wife loves it, she joins us sometimes too but I love this, I can see how much you love each other and it's beautiful that you've taken it physical."
Laura blinked a few times before she replied.
"I found out like, a day before we were coming here that my ex was cheating on me. I couldn't bear not to come on this trip so I asked Marcus, I didn't know it would go this far I really didn't. You've seriously done the same?"
"Yes, I could see it in your eyes, I have this gift of knowing people are in love before they do. If you'd told me straight out, 'he's my brother' I may not have pushed but I'm happy for you both I really am."
"So the whole truth or dare was to steer us that way?" I asked.
"In a way, not fond of that game to be honest but I wanted to see if you would keep pretending. As far as anyone else here goes, you're a couple and I promise I won't push anymore. Doesn't look like I have to though do I?" said Maya.
"No, he was amazing, I'm going to teach him how I like my pussy to be eaten tonight and I can't wait to take him in our own beds," Said Laura then she kissed me.
"Great, now I have to walk with this lump in my shorts thinking about that." We all laughed.
"Well, when we get back to the resort I may let that waiter that's been flirting with me fuck my brains out for our last two days, now that I won't feel guilty about ghosting you two," said Maya with a grin.
"Oooh, the cute one with biceps like logs?" said Laura.
"That's him, fucking better not be a sock in his pants, all I'm saying."
Laura and I spent the last two days in bed making love, when it was time to part ways with Maya at the airport we each hugged her close.
"Thank you for what you've given us Maya, I'm sure without you we'd never have taken this leap and just fantasized about it separately," said Laura.
"Just be careful okay, not everyone is as open minded and just as kinky as I am," she replied.
"Thank you Maya," I said and kissed her on the cheek.
"Hey, you're mine mister," said Laura, we laughed.
The flight home was okay, Mom and Dad were there to meet us at the airport.
"Well, did you have a good time, was Marcus okay for you sweetie?" Said Mom as we drove home.
"Yes, he was wonderful, he made the trip enjoyable and I didn't feel like I forced him to go at all," replied Laura.
"Good, well we can talk about it all later, I'm sure you're tired."
Oh she has no idea, I thought to myself, trying not to laugh.
Laura and I continued our fun when we got home but that's a story for another time...